#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:07:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178550 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/57/4065753.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4065753
loop_
_publ_author_name
'Ghereg, Dumitru'
'André, Erwan'
'Ech-Cherif El Kettani, Sakina'
'Saffon, Nathalie'
'Lazraq, Mohamed'
'Ranaivonjatovo, Henri'
'Gornitzka, Heinz'
'Miqueu, Karinne'
'Sotiropoulos, Jean-Marc'
'Escudié, Jean'
_publ_section_title
;
 Reactions of Germenes with Somepara-Quinones: Formation of a Tricyclic
 Compound from 1,4-Benzoquinone Undergoing an Unexpected
 Rearrangement†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              4849
_journal_paper_doi               10.1021/om100113c
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C78 H88 Ge2 O2'
_chemical_formula_weight         1202.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.855(6)
_cell_angle_beta                 90.973(6)
_cell_angle_gamma                107.554(7)
_cell_formula_units_Z            1
_cell_length_a                   9.1256(15)
_cell_length_b                   13.234(2)
_cell_length_c                   15.561(3)
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1617.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10216
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         5.14
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_correction_T_min  0.7585
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0925P)²+0.3921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                2579
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100113c_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4065753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.83418(8) 0.21179(7) 0.28418(5) 0.0399(3) Uani 1 1 d . . .
O1 O 1.0204(5) 0.3315(4) 0.3277(3) 0.0392(12) Uani 1 1 d . . .
C1 C 0.8085(8) 0.2423(6) 0.4834(4) 0.0364(17) Uani 1 1 d . . .
C2 C 1.1462(8) 0.5001(6) 0.4696(4) 0.0374(18) Uani 1 1 d . . .
H2 H 1.2436 0.5016 0.4486 0.045 Uiso 1 1 calc R . .
C3 C 0.5914(7) 0.2516(6) 0.4077(5) 0.0344(17) Uani 1 1 d . . .
C4 C 0.7662(7) 0.2816(6) 0.4113(4) 0.0344(17) Uani 1 1 d . . .
C6 C 0.4699(9) 0.1416(8) 0.0775(5) 0.052(2) Uani 1 1 d . . .
H6 H 0.3743 0.0792 0.0469 0.062 Uiso 1 1 calc R . .
C7 C 1.0200(7) 0.4206(6) 0.4125(5) 0.0361(17) Uani 1 1 d . . .
C8 C 0.5396(8) 0.1918(6) 0.4639(5) 0.0407(18) Uani 1 1 d . . .
C9 C 0.7101(8) 0.2254(6) 0.1876(4) 0.0394(18) Uani 1 1 d . . .
C10 C 0.6755(8) 0.1888(6) 0.5136(5) 0.0409(18) Uani 1 1 d . . .
C11 C 1.1448(7) 0.5884(6) 0.5659(4) 0.0370(18) Uani 1 1 d . . .
H11 H 1.1960 0.5702 0.6125 0.044 Uiso 1 1 calc R . .
C12 C 0.7522(9) 0.3206(7) 0.1628(5) 0.048(2) Uani 1 1 d . . .
C13 C 0.8470(8) -0.0207(7) 0.2588(5) 0.047(2) Uani 1 1 d . . .
C14 C 1.0005(8) 0.0684(7) 0.1671(5) 0.049(2) Uani 1 1 d . . .
C15 C 0.6854(10) 0.1438(7) 0.5789(5) 0.054(2) Uani 1 1 d . . .
H15 H 0.5940 0.1079 0.5986 0.065 Uiso 1 1 calc R . .
C16 C 0.5668(8) 0.1337(7) 0.1437(5) 0.046(2) Uani 1 1 d . . .
C17 C 0.9013(9) -0.1162(7) 0.2196(5) 0.051(2) Uani 1 1 d . . .
H17 H 0.8679 -0.1788 0.2379 0.062 Uiso 1 1 calc R . .
C18 C 0.8946(8) 0.0711(6) 0.2337(4) 0.0371(18) Uani 1 1 d . . .
C19 C 0.4860(8) 0.2739(6) 0.3589(5) 0.0450(19) Uani 1 1 d . . .
H19 H 0.5205 0.3161 0.3219 0.054 Uiso 1 1 calc R . .
C20 C 0.3303(8) 0.2339(7) 0.3648(5) 0.053(2) Uani 1 1 d . . .
H20 H 0.2579 0.2518 0.3338 0.063 Uiso 1 1 calc R . .
C21 C 1.0565(9) 0.1636(7) 0.1339(5) 0.058(2) Uani 1 1 d . . .
H21A H 1.1256 0.2354 0.1863 0.087 Uiso 1 1 calc R . .
H21B H 0.9669 0.1791 0.1130 0.087 Uiso 1 1 calc R . .
H21C H 1.1133 0.1385 0.0807 0.087 Uiso 1 1 calc R . .
C22 C 0.5064(10) 0.2347(8) 0.0549(5) 0.055(2) Uani 1 1 d . . .
C23 C 0.9543(8) 0.2524(6) 0.5209(5) 0.0454(19) Uani 1 1 d . . .
H23 H 1.0462 0.2895 0.5023 0.054 Uiso 1 1 calc R . .
C24 C 0.5105(8) 0.0310(7) 0.1676(5) 0.053(2) Uani 1 1 d . . .
H24A H 0.4936 0.0583 0.2340 0.080 Uiso 1 1 calc R . .
H24B H 0.5886 -0.0079 0.1585 0.080 Uiso 1 1 calc R . .
H24C H 0.4125 -0.0245 0.1258 0.080 Uiso 1 1 calc R . .
C25 C 0.2773(9) 0.1679(7) 0.4152(6) 0.058(2) Uani 1 1 d . . .
H25 H 0.1687 0.1353 0.4138 0.070 Uiso 1 1 calc R . .
C26 C 0.7312(9) -0.0286(7) 0.3271(5) 0.056(2) Uani 1 1 d . . .
H26A H 0.7871 -0.0083 0.3893 0.083 Uiso 1 1 calc R . .
H26B H 0.6567 -0.1087 0.3019 0.083 Uiso 1 1 calc R . .
H26C H 0.6752 0.0262 0.3340 0.083 Uiso 1 1 calc R . .
C27 C 0.3808(8) 0.1497(7) 0.4669(5) 0.052(2) Uani 1 1 d . . .
H27 H 0.3451 0.1088 0.5047 0.063 Uiso 1 1 calc R . .
C28 C 1.0025(10) -0.1195(8) 0.1549(5) 0.055(2) Uani 1 1 d . . .
C29 C 0.6476(10) 0.3222(7) 0.0966(5) 0.055(2) Uani 1 1 d . . .
H29 H 0.6756 0.3864 0.0800 0.066 Uiso 1 1 calc R . .
C30 C 1.0503(9) -0.0287(8) 0.1299(5) 0.058(2) Uani 1 1 d . . .
H30 H 1.1204 -0.0315 0.0852 0.069 Uiso 1 1 calc R . .
C31 C 0.9042(9) 0.4221(7) 0.2026(6) 0.063(2) Uani 1 1 d . . .
H31A H 0.9038 0.4717 0.2694 0.095 Uiso 1 1 calc R . .
H31B H 0.9166 0.4685 0.1659 0.095 Uiso 1 1 calc R . .
H31C H 0.9907 0.3918 0.1984 0.095 Uiso 1 1 calc R . .
C32 C 0.9620(10) 0.2072(7) 0.5859(5) 0.058(2) Uani 1 1 d . . .
H32 H 1.0615 0.2140 0.6118 0.070 Uiso 1 1 calc R . .
C33 C 0.8310(11) 0.1519(8) 0.6155(5) 0.063(2) Uani 1 1 d . . .
H33 H 0.8407 0.1205 0.6596 0.076 Uiso 1 1 calc R . .
C34 C 1.0594(12) -0.2241(8) 0.1112(6) 0.087(3) Uani 1 1 d . . .
H34A H 1.0555 -0.2477 0.0426 0.131 Uiso 1 1 calc R . .
H34B H 0.9925 -0.2897 0.1222 0.131 Uiso 1 1 calc R . .
H34C H 1.1668 -0.2020 0.1408 0.131 Uiso 1 1 calc R . .
C35 C 0.3986(10) 0.2426(9) -0.0161(6) 0.083(3) Uani 1 1 d . . .
H35A H 0.3971 0.3230 0.0077 0.125 Uiso 1 1 calc R . .
H35B H 0.2932 0.1886 -0.0243 0.125 Uiso 1 1 calc R . .
H35C H 0.4362 0.2212 -0.0775 0.125 Uiso 1 1 calc R . .
C36 C 0.710(3) 0.454(3) 0.9183(18) 0.164(11) Uani 0.479(15) 1 d PDU A 1
H36A H 0.6499 0.5081 0.9392 0.246 Uiso 0.479(15) 1 calc PR A 1
H36B H 0.8195 0.4994 0.9244 0.246 Uiso 0.479(15) 1 calc PR A 1
H36C H 0.6995 0.4116 0.9578 0.246 Uiso 0.479(15) 1 calc PR A 1
C37 C 0.648(4) 0.369(2) 0.8161(19) 0.163(10) Uani 0.479(15) 1 d PDU A 1
H37A H 0.7154 0.3910 0.7729 0.195 Uiso 0.479(15) 1 calc PR A 1
H37B H 0.6391 0.2880 0.8056 0.195 Uiso 0.479(15) 1 calc PR A 1
C38 C 0.491(3) 0.379(3) 0.8024(19) 0.188(10) Uani 0.479(15) 1 d PDU A 1
H38A H 0.4626 0.4277 0.8625 0.226 Uiso 0.479(15) 1 calc PR A 1
H38B H 0.4078 0.3023 0.7691 0.226 Uiso 0.479(15) 1 calc PR A 1
C39 C 0.538(3) 0.443(3) 0.739(2) 0.155(9) Uani 0.479(15) 1 d PDU A 1
H39A H 0.6161 0.4176 0.6999 0.186 Uiso 0.479(15) 1 calc PR A 1
H39B H 0.5765 0.5293 0.7758 0.186 Uiso 0.479(15) 1 calc PR A 1
C40 C 0.376(3) 0.396(2) 0.680(2) 0.151(12) Uani 0.479(15) 1 d PDU A 1
H40A H 0.3688 0.3286 0.6205 0.227 Uiso 0.479(15) 1 calc PR A 1
H40B H 0.3585 0.4579 0.6666 0.227 Uiso 0.479(15) 1 calc PR A 1
H40C H 0.2967 0.3718 0.7165 0.227 Uiso 0.479(15) 1 calc PR A 1
C36' C 0.730(3) 0.441(4) 0.856(3) 0.180(12) Uani 0.521(15) 1 d PDU A 2
H36D H 0.8025 0.4181 0.8124 0.270 Uiso 0.521(15) 1 calc PR A 2
H36E H 0.6835 0.3791 0.8767 0.270 Uiso 0.521(15) 1 calc PR A 2
H36F H 0.7868 0.5143 0.9120 0.270 Uiso 0.521(15) 1 calc PR A 2
C37' C 0.608(3) 0.458(2) 0.8081(18) 0.133(7) Uani 0.521(15) 1 d PDU A 2
H37C H 0.5491 0.4969 0.8564 0.159 Uiso 0.521(15) 1 calc PR A 2
H37D H 0.5348 0.3805 0.7637 0.159 Uiso 0.521(15) 1 calc PR A 2
C38' C 0.6610(19) 0.5304(18) 0.7532(13) 0.100(6) Uani 0.521(15) 1 d PDU A 2
H38C H 0.6324 0.6021 0.7724 0.120 Uiso 0.521(15) 1 calc PR A 2
H38D H 0.7683 0.5415 0.7385 0.120 Uiso 0.521(15) 1 calc PR A 2
C39' C 0.539(3) 0.418(2) 0.6883(18) 0.152(10) Uani 0.521(15) 1 d PDU A 2
H39C H 0.5844 0.3735 0.6344 0.183 Uiso 0.521(15) 1 calc PR A 2
H39D H 0.5009 0.3693 0.7233 0.183 Uiso 0.521(15) 1 calc PR A 2
C40' C 0.409(3) 0.4398(17) 0.6522(18) 0.078(7) Uani 0.521(15) 1 d PDU A 2
H40D H 0.3174 0.4139 0.6797 0.117 Uiso 0.521(15) 1 calc PR A 2
H40E H 0.3862 0.3963 0.5827 0.117 Uiso 0.521(15) 1 calc PR A 2
H40F H 0.4370 0.5239 0.6699 0.117 Uiso 0.521(15) 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Ge1 C18 103.3(2) . .
O1 Ge1 C9 110.2(3) . .
C18 Ge1 C9 113.3(3) . .
O1 Ge1 C4 90.0(2) . .
C18 Ge1 C4 126.7(3) . .
C9 Ge1 C4 109.4(3) . .
C7 O1 Ge1 112.3(4) . .
C23 C1 C10 119.4(6) . .
C23 C1 C4 129.4(6) . .
C10 C1 C4 111.1(5) . .
C7 C2 C11 123.2(6) . .
C19 C3 C8 120.0(6) . .
C19 C3 C4 130.0(6) . .
C8 C3 C4 110.0(6) . .
C1 C4 C3 102.1(5) . .
C1 C4 C11 114.9(5) . 2_766
C3 C4 C11 114.3(5) . 2_766
C1 C4 Ge1 115.2(4) . .
C3 C4 Ge1 114.6(4) . .
C11 C4 Ge1 96.4(4) 2_766 .
C22 C6 C16 123.1(8) . .
C2 C7 O1 123.7(6) . .
C2 C7 C11 124.3(6) . 2_766
O1 C7 C11 111.9(5) . 2_766
C27 C8 C3 119.9(7) . .
C27 C8 C10 131.3(7) . .
C3 C8 C10 108.7(6) . .
C12 C9 C16 119.4(6) . .
C12 C9 Ge1 124.7(5) . .
C16 C9 Ge1 115.9(6) . .
C15 C10 C1 121.6(6) . .
C15 C10 C8 130.7(7) . .
C1 C10 C8 107.7(6) . .
C2 C11 C7 112.4(5) . 2_766
C2 C11 C4 116.4(5) . 2_766
C7 C11 C4 107.5(5) 2_766 2_766
C29 C12 C9 118.6(7) . .
C29 C12 C31 117.2(7) . .
C9 C12 C31 124.3(6) . .
C18 C13 C17 120.8(7) . .
C18 C13 C26 123.4(7) . .
C17 C13 C26 115.8(7) . .
C30 C14 C18 117.9(8) . .
C30 C14 C21 119.3(7) . .
C18 C14 C21 122.8(7) . .
C10 C15 C33 119.2(8) . .
C6 C16 C9 118.4(8) . .
C6 C16 C24 118.5(7) . .
C9 C16 C24 123.1(6) . .
C28 C17 C13 120.4(8) . .
C13 C18 C14 119.0(7) . .
C13 C18 Ge1 125.8(5) . .
C14 C18 Ge1 115.2(6) . .
C20 C19 C3 119.0(7) . .
C19 C20 C25 121.3(7) . .
C6 C22 C29 117.9(7) . .
C6 C22 C35 122.3(8) . .
C29 C22 C35 119.7(8) . .
C32 C23 C1 118.2(7) . .
C27 C25 C20 120.2(7) . .
C25 C27 C8 119.5(8) . .
C30 C28 C17 119.1(7) . .
C30 C28 C34 120.6(8) . .
C17 C28 C34 120.3(9) . .
C22 C29 C12 122.7(8) . .
C28 C30 C14 122.8(8) . .
C23 C32 C33 123.2(7) . .
C32 C33 C15 118.4(7) . .
C38 C37 C36 102.0(17) . .
C37 C38 C39 94.2(17) . .
C38 C39 C40 96.1(16) . .
C36' C37' C38' 116(2) . .
C39' C38' C37' 72.0(17) . .
C40' C39' C38' 111(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 O1 1.824(4) .
Ge1 C18 1.960(7) .
Ge1 C9 1.964(7) .
Ge1 C4 2.015(6) .
O1 C7 1.369(7) .
C1 C23 1.391(8) .
C1 C10 1.403(9) .
C1 C4 1.501(9) .
C2 C7 1.305(9) .
C2 C11 1.484(8) .
C3 C19 1.384(9) .
C3 C8 1.401(9) .
C3 C4 1.517(8) .
C4 C11 1.549(9) 2_766
C6 C22 1.364(11) .
C6 C16 1.403(9) .
C7 C11 1.527(8) 2_766
C8 C27 1.396(9) .
C8 C10 1.470(9) .
C9 C12 1.411(10) .
C9 C16 1.411(9) .
C10 C15 1.383(9) .
C11 C7 1.527(8) 2_766
C11 C4 1.549(9) 2_766
C12 C29 1.403(9) .
C12 C31 1.511(10) .
C13 C18 1.374(10) .
C13 C17 1.407(10) .
C13 C26 1.523(10) .
C14 C30 1.398(10) .
C14 C18 1.426(9) .
C14 C21 1.505(10) .
C15 C33 1.393(10) .
C16 C24 1.497(10) .
C17 C28 1.374(10) .
C19 C20 1.377(10) .
C20 C25 1.387(10) .
C22 C29 1.374(11) .
C22 C35 1.522(10) .
C23 C32 1.378(10) .
C25 C27 1.366(10) .
C28 C30 1.361(11) .
C28 C34 1.528(10) .
C32 C33 1.393(11) .
C36 C37 1.502(19) .
C37 C38 1.499(19) .
C38 C39 1.52(2) .
C39 C40 1.537(19) .
C36' C37' 1.458(18) .
C37' C38' 1.505(18) .
C38' C39' 1.49(2) .
C39' C40' 1.456(18) .
